Holden has time to spare before Sally arrives, especially since she’s always late. As he waits, he looks at the many attractive women who pass him by, and though this entertains him, he can’t help but think about how they’ll probably all grow up to marry boring men. He then ruminates on what it means to be boring, concluding that some boring people aren’t so bad, since most people have hidden talents that might redeem them. When Sally finally arrives, Holden can’t stay mad at her for being late because she looks so good. However, he gets annoyed at the sound of her voice and the “phony” words she chooses. Nonetheless, though, he focuses on how attractive she is, feeling glad that he decided to call her.
Even if it’s true that Holden is often hard-headed, stubborn, or unfair to the people in his life, it’s hard to deny that he’s rather complex. As he looks around at the women passing him while he waits for Sally, he is both critical and sympathetic, imagining their future lives and eventually demonstrating his ability to empathize with individuals who most people hardly think about. This sympathetic worldview quickly shatters, though, when Sally arrives and Holden immediately finds her annoying but still shallowly embraces her simply because of her good looks.
On the cab ride to the theater, Holden convinces Sally to “horse around” with him, though she doesn’t want to at first because—according to Holden—she doesn’t want to mess up her lipstick. After they kiss for a while, Holden suddenly decides that he wants to marry her, and he blurts out that he loves her. “Oh, darling, I love you too,” Sally responds before telling him that he should let his hair grow out. This annoys Holden, but he doesn’t say anything.
This is the first time in the novel that Holden has actually made a genuine effort to connect with another person. When he does this, his emotions suddenly fly out of control, and he overstates his feelings for Sally. This suggests that he’s in desperate need of human connection. The instant he receives this kind of attention, then, he gushes with appreciation. And yet, he immediately returns to his normal state of cynicism when Sally says something that strikes him as annoying—indicating that he isn’t quite as enthralled with her as he thinks. Instead, he has simply found a way to idealize her, even though he already thinks of her as imperfect.
Holden doesn’t find the play as bad as he expected it to be, but he still thinks it’s “on the crappy side.” The actors’ performances seem phony and conceited to him, but Sally loves it. During the first intermission, she runs into a boy she once met at another school, and they spend the entirety of the intermission talking about the play. The way they converse disgusts Holden, especially when the boy refers to the actors as “angels,” but there’s nothing he can do to stop them from talking. To his horror, he also has to endure their “phony” conversation during the second intermission. By the time Holden and Sally finally leave the boy behind after the play, Holden feels as if he hates Sally, though he agrees to go ice-skating at Radio City when she enthusiastically proposes the idea.
Anyone who seems self-confident or comfortable in society strikes Holden as “phony,” so it’s no surprise that he strongly dislikes the boy Sally talks to during intermission. To make matters worse, he also resents this young man for encroaching upon his time with Sally, since he has been desperate for human interaction—so desperate, in fact, that he agrees to go ice-skating with Sally even though he has decided that he hates her.
Holden suspects that Sally only wants to go skating because the rink gives girls a small dress to wear. And though it annoys him that Sally purposefully walks in front of him so he can see how her behind looks in this dress, he can’t deny that she looks good in it. When they finally get on the ice, it becomes clear that they’re both terrible skaters, so they soon retire to a small bar-restaurant near the rink, where Holden tries to order a scotch and soda but ends up having to order Coke. As they sit there, Sally asks if he’s going to come over on Christmas Eve to help her trim the tree—an invitation she extended in a letter to which he claims to have responded. Irritated, Holden tells her that he’s going to come.
Holden’s conflicted feelings about women arise once again, as he struggles to interpret Sally’s behavior. Even if he’s right that Sally only wants to go ice-skating so that Holden will see her behind in the small dress, one would think that this would flatter him. Instead, though, he finds her actions somehow irritating, perhaps because he doesn’t really want to pursue a romantic relationship with her, despite his previous declaration that he loves her. In this way, he once again delays his foray into the adult world of romance.
On edge because of the play and because of Sally’s question about Christmas Eve, Holden suddenly leans forward and asks if she ever gets fed up with stuff like school. She admits that she’s often bored in class, but he presses on, saying that this isn’t what he means. He says he hates school and everything else: taxis, New York, phony guys like the one they met at the play, having to take elevators, going to the tailor—as he goes on, Sally interrupts him and asks him not to shout, which he finds funny because he isn’t raising his voice. Still, he goes on, saying that he never wants to become the kind of person who cares about his car. He also says that he’s only in New York because of Sally and would otherwise be off in a cabin in the woods.
In many ways, Holden’s disillusionment is typical for a teenager trying to figure out his place in the world. However, that he finds such nonconsequential matters (like the existence of taxis, for instance) so irritating suggests that he’s dealing with something more serious than regular teenage angst. Perhaps recognizing that Holden is disproportionately upset with everyday life, Sally asks him to calm down, but he fails to see why she doesn’t share his misgivings about life. In turn, he alienates himself from her even though it’s clear that he needs somebody to help him address his negative feelings, which are characteristic of true depression.
Holden tells Sally that she should try going to a boys’ school sometime, since boys’ schools are “full of phonies.” The only point of these schools, he argues, is to someday lead the kind of life that might allow you to buy a Cadillac. He also laments the ways in which other students group together according to various categories, pointing out that all the Catholics and athletes and academics always flock to one another. Seizing on the idea of leaving New York, he suggests that he and Sally should run away to New England and live in a cabin together. They could get married, he says, and he could find a job and chop wood to stay warm in the winter. “You can’t just do something like that,” Sally says, annoyed by his enthusiasm. She then asks him to stop yelling, even though he insists that he’s being quiet.
Listing the ways in which he feels isolated from his peers at every boys’ school he’s attended, Holden tries to express his disillusionment with the idea that everyone has to play the game of life by a certain set of rules. Unlike everyone else, Holden is uninterested in following the rules because he has no desire to achieve the various goals that people assume all young men want to achieve. This is why he proposes that he and Sally elope to New England. In response, Sally says, “You can’t just do something like that,” thereby aligning herself with the kind of people who think that there are certain rules everyone must follow. To step outside of these rules, she thinks, is simply not an option.
Sally reminds Holden that they’re too young to go off on their own, insisting that they’ll have plenty of time in life to do whatever they want. This, Holden says, is exactly the point—by the time they’re adults, they won’t want to pick up and escape to the cabins of New England. By then, he argues, they’ll have too many obligations and will be wrapped up in the monotonous ins and outs of everyday life. He then says that Sally doesn’t understand him, and she agrees with this statement, adding that he probably doesn’t even understand himself. In response, he calls her a “royal pain in the ass,” and she begins to cry. Holden quickly apologizes, but also can’t keep himself from laughing. She then tells him to leave, so he listens to her, thinking as he goes that he probably wouldn’t have wanted to elope with her anyway.
During this exchange, it becomes clear that Holden is afraid of succumbing to what he perceives as the mundane reality of adulthood. Although he’s adamant about never becoming a phony, he obviously thinks that he will inevitably lead a boring and uninspired life someday. Consequently, he wants to do anything he can to avoid this fate, which is why he’s willing to break all of life’s supposed rules. However, lashing out at Sally is no way to achieve this, which is why he winds up alone and unhappy once again as he leaves Sally at the restaurant.